I’m going to answer the questions here publicly because I think it is important to declare your intentions. I am writing this blog now in large part as a record, to be honest and open, and then in a few years time I can look back over all the things I believed and think: “Why did I think that?”
What do you want to do? (Not your job, but your work, now, tomorrow, and in the future?
I want to work on projects that are about changing people for the better, and I always want to have a hand in teaching young people. That might mean a video that gets people talking about a subject that they are usually afraid to talk about, or coaching a group of people to have some new ideas. It might be teaching kids like I have been for the past 4 years, but not just teaching English in Japan. I’ve never been more excited in my life than after I quit my job and realised I could do whatever I wanted, so I don’t want to go back to a standard 5-day-week 9am-5pm (or Japanese 8am-7pm) ever again, even if I have to work more than that to make sure I’m not just a cog in a machine.
Who do you want to change, and how do you want to change them?
I want to change people who feel like I used to: like there isn’t any way to get paid well for doing something I enjoy, like I have to work 40 hours a week and only take a few weeks off every now and then to travel, when really I would rather travel and live anywhere I please. I want to help people realise that the rules have changed and the old rule-book needs to be rewritten. But rather than this being a terrible thing where we need to get back to the old days where everyone could get a college degree and get a job, no questions asked, this is actually an amazing opportunity to do something incredible and different and tread new ground.
How much risk? (from 1 [a little] to 10 [bet everything]), how much are you willing to put at stake to make the change you seek?
I’d say a solid 8. While I still need to make a living, I quit my job in March to go part-time, though I’m still working a few jobs to help keep me in my house.
How much work are you willing to do to get there? Be specific about the tradeoffs.
I’ll do whatever it takes to get there, as long as the goal is to reduce the amount of time I need to spend following orders and doing busywork. I can work all day on something I’m passionate about, but tell me that I need to work all day on something or I’m fired and I’ll do terrible work.
Does this project matter enough for the risk and the effort you’re putting into it?
Is it possible — has anyone with your resources ever pulled off anything like this?
Probably, but that’s part of the fun, right? I’m sure there are tons of people out there who are doing something similar to what I’m doing, but probably not exactly the same.